Acetic Acid → 6-(4-Chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-3-dimethylamino-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione

HRID 1994397Notes

Reaction equation

HRID 1994397 reaction equation
Br.[Cl:2][C:3]1[CH:36]=[CH:35][C:6]([CH2:7][CH:8]2[N:13]3C(=O)C(N)[CH2:16][N:17]([S:18]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=4[Cl:28])(=[O:20])=[O:19])[CH:12]3[CH2:11][N:10]([CH:31]([CH3:33])[CH3:32])[C:9]2=[O:34])=[CH:5][CH:4]=1.[C:37]([OH:40])(=O)[CH3:38].[CH2:41]=O.[C:43]([BH3-])#[N:44].[Na+]>CO.C1COCC1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8]2[N:13]3[C:37](=[O:40])[CH:38]([N:44]([CH3:43])[CH3:41])[CH2:16][N:17]([S:18]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=4[Cl:28])(=[O:20])=[O:19])[CH:12]3[CH2:11][N:10]([CH:31]([CH3:32])[CH3:33])[C:9]2=[O:34])=[CH:35][CH:36]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 686934646-(4-Chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-3-amino-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione hydrobromide

Product 1

HCID 591342116-(4-Chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-3-dimethylamino-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

200 mg of 6-(4-chlorobenzyl)-1-(2,4-dichlorobenzenesulfonyl)-3-amino-8-isopropylhexahydropyrazino[1,2-a]pyrimidine-4,7-dione hydrobromide (Example 2) were dissolved in 15 ml of methanol, and 600 μl of acetic acid were added. 0.5 ml of 37% strength aqueous formaldehyde and 3 ml of 1M sodium cyanoborohydride solution in THF were added to this solution. After 2 hours, the reaction mixture was evaporated, suspended in 5% Et3N in ethyl acetate and filtered through a small silica gel column. The eluent was evaporated, and the crude substance was dissolved in a mixture of acetonitrile and water and freeze dried. The pure title compound was removed after purification by HPLC. The system and process described under “general processes” was used for this. MW=586.10 (calculated, monoisotopic); measured value (M+H)+: 587.3.

Workup

  1. customthe reaction mixture was evaporated
  2. filtrationfiltered through a small silica gel column
  3. customThe eluent was evaporated
  4. dissolutionthe crude substance was dissolved in a mixture of acetonitrile and water and freeze
  5. customdried
  6. customThe pure title compound was removed
  7. customafter purification by HPLC

Sources & evidence

ORD record
ord-dd8ab89909724d3a9861e42470417e72
Source dataset
uspto-grants-2010_01
Patent number
US07652007B2

Reaction notes

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